Dimethyl Sulfoxide → HCID 12968706, Verbindung

Temperatur

70 °C

To a solution of trifluoro-methanesulfonic acid 4-[1-benzyl-3-(3-methoxy-phenyl)-piperidin-3-yl]-phenyl ester (12.9 g, 25.4 mmol) in a Parr pressure bottle in MeOH (39 mL) were added DMSO (18 mL) and triethylamine (21 mL, 151 mmol). To the reaction mixture were added palladium acetate (3.99 g, 17.8 mmol) and 1,3-bis (diphenylphosphino) propane (5.25 g, 12.3 mmol). The mixture was shaken under 40 psi of CO at 70° C. for 4 hours. The reaction mixture was cooled to room temperature and was diluted with diethyl ether (600 mL). The ether layer was washed with water (5×60 mL), dried (MgSO4) and concentrated. The crude residue was purified by flash chromatography with hexanes/EtOAc (3:1) to afford 9.82 g of 4-[1-benzyl-3-(3-methoxy-phenyl)-piperidin-3-yl]-benzoic acid methyl ester. 1HNMR (400 MHz, CDCl3) δ 7.87 (d, 2H), 7.41-7.20 (comp, 7H), 7.12 (t, 1H), 6.77 (s, 1H), 6.73(d, 1H) 6.66 (d, 1H), 3.86 (s, 3H), 3.71 (s, 3H), 3.51 (s, 2H), 3.05 (br, 1H), 2.68 (br, 1H), 2.55 (br, 1H), 2.41-2.24 (comp, 2H), 2.22-2.18 (m, 1H), 1.61-1.42 (comp, 2H); MS (M+1) 416.3.

1. temperatureThe reaction mixture was cooled to room temperature
2. washThe ether layer was washed with water (5×60 mL)
3. dry with materialdried (MgSO4)
4. concentrationconcentrated
5. customThe crude residue was purified by flash chromatography with hexanes/EtOAc (3:1)

ORD-Eintrag

ord-237ba27e45c04bdba90ab4c5b4776e83

Quelldatensatz

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06503905B1